Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides

van der Wal, S., Capicciotti, C. J., Rontogianni, S., Ben, R. N. and Liskamp, R. M.J. (2014) Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides. MedChemComm, 5(8), pp. 1159-1165. (doi: 10.1039/c4md00013g)

Abstract

Antifreeze glycoproteins (AFGPs) are important naturally occurring biological antifreezes that lower the freezing point of a solution, thereby preventing uncontrolled ice growth. These compounds also inhibit ice recrystallization. Described in this paper is a synthetic antifreeze glycopeptide-based polymer synthesized from an azide/alkyne glycopeptide building block by partial reduction of the azide and subsequent copper catalyzed azide alkyne cycloaddition (CuAAC) polymerization to obtain linear oligomers. To compare the activity with native AFGPs, a linear dodecapeptide (oligomer with four repeating units) was synthesized and isolated which had a comparable length to AFGP-8, the lowest molecular mass glycoprotein AFGP found in nature. In terms of ice recrystallization inhibition (IRI) activity, the triazole-based oligomers displayed only modest IRI activity compared with AFGP-8 and a previously described carbon-linked AFGP analogue. However, CD spectroscopy showed that the triazole-based tetramer possessed a similar secondary structure to the related amide based carbon-linked AFGP tetramer based on AFGP-8.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: van der Wal, S., Capicciotti, C. J., Rontogianni, S., Ben, R. N., and Liskamp, R. M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: MedChemComm
• Publisher: R S C Publications
• ISSN: 2040-2503
• ISSN (Online): 2040-2511